Quantum-chemical study of the activity of glycine, threonine and their dipeptides in relation to free radicals
DOI:
https://doi.org/10.33581/2520-257X-2026-1-%25pKeywords:
glycine, threonine, dipeptides, threonyl-threonine, cyclo(di(threonine)), antiradical activity, density functional theory, quantum-chemical calculationAbstract
A methodology for quantum-chemical studies of the antioxidant activity of compounds of various nature has been developed. Reactivity of glycine, threonine and their dipeptides with respect to active species obtained in test systems using peroxyl radicals ${\text{(RO}}{{\text{O}}^ \bullet })$ and cation radicals of 2,2¢-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) ${\text{(ABT}}{{\text{S}}^{ \bullet {\text{ + }}}})$ has been compared with the results of calculations. The most probable sites of hydrogen atom abstraction from amino acids and dipeptides molecules in the gas phase and aqueous solution has been determined by calculating the thermodynamic characteristics of the corresponding radicals. To assess the tendency of compounds to exhibit antioxidant activity via the hydrogen atom transfer mechanism, the Gibbs energies of reactions with \[{\text{HO}}_{\text{2}}^ \bullet \], ${\text{RO}}{{\text{O}}^ \bullet }$ and \[{\text{H}}{{\text{O}}^ \bullet }\] radicals, as well as the activation barriers for the thermodynamically most favourable processes of hydrogen atom abstraction by the \[{\text{HO}}_{\text{2}}^ \bullet \] radical, has been calculated. The ability of the compounds to exhibit antioxidant activity via the single electron transfer mechanism has been assessed by calculating adiabatic ionisation potentials and the energies of the highest occupied molecular orbital. The antioxidant activity series of the studied compounds, constructed based on the calculated descriptors, are consistent with experimental data. Analysis of the electron density distribution in molecules and radicals has made it possible to explain the experimentally observed differences in the antioxidant activity of glycine, glycyl-glycine, threonine and its linear and cyclic dipeptides.
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